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Neoandrographolide

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-N2001

  • Specification : 98%

  • CAS number : 27215-14-1

  • Formula : C26H40O8

  • Molecular Weight : 480.59

  • PUBCHEM ID : 9848024

  • Volume : 20mg

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Catalogue Number

BF-N2001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

480.59

Appearance

White crystalline powder

Botanical Source

Andrographis paniculata

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)O

Synonyms

2(5H)-Furanone, 3-[2-[(1R,4aS,5R,8aS)-5-[(β-D-glucopyranosyloxy)methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-neo-Andrographolide/{(1R,4aS,5R,8aS)-1,4a-Dimethyl-6-methylene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]decahydronaphthalen-1-yl}methyl β-D-glucopyranoside/{(1R,4aS,5R,8aS)-1,4a-Dimethyl-6-methylene-5-[2-(2-oxo-2,5-dihydro-3-furanyl)ethyl]decahydro-1-naphthalenyl}methyl β-D-glucopyranoside/neoandrographoside/Neoandrographolid/ANDROGRAPHOLIDE,NEO

IUPAC Name

4-[2-[(1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one

Density

1.3±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

220.1±25.0 °C

Boiling Point

668.1±55.0 °C at 760 mmHg

Melting Point

167-168ºC

InChl

InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17?,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1

InChl Key

YGCYRQKJYWQXHG-JXAGCRMJSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:27215-14-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31260057

Abstract

“Andrographis paniculata is an important traditional Chinese herbal material widely used for treatment of fever and diarrhea. The three diterpenoids [andrographolide (AP), dehydroandrographolide (DP) and neoandrographolide (NP)] in A. paniculata were characterized as the key active components for its extractive and related medicinal preparations. A rapid and accurate quantitative analysis of these three diterpenoids in A. paniculata capsules was accomplished by means of a valid and reliable high-performance liquid chromatography with tandem mass spectrometric (HPLC-MS/MS) analytical method. An optimized gradient elution method, which under the mobile phase consisting of methanol and water, was established successfully. An XDB C18 column (3.5 μm, 2.1 mm × 50 mm) was successfully applied to separate these three diterpenoids at the flow rate of 0.55 mL/min. A triple quadrupole mass spectrometer with multiple reaction monitoring (MRM) mode using an electrospray ionization source was served for analytical detection. The linearity, specificity, accuracy, recovery, precision, stability and repeatability were demonstrated to fully confirm the validity of this study. Good linear regression relationships for the three analytes were obtained over the range of 0.50-1000 ng/mL. Intra-day and inter-day precisions were evaluated with relative standard deviation < 7.62%, and the extraction recovery varied from 93.8% to 102.0%. The rapid and accurate HPLC-MS/MS analytical method was developed for the quality evaluation of A. paniculata capsules successfully. The content of AP, DP and NP obtained were 3.90-4.08, 4.77-5.04, 4.32-4.48 mg/g in A. paniculata capsules, respectively. Moreover, it is expected that this analytical technique can be applied to detect three effective components rapidly and accurately in other different medicinal preparations of A. paniculata as a method for their quality control.
© The Author(s) 2019. Published by Oxford University Press. All rights reserved. For permissions, please email: journals.permissions@oup.com.”

Title

Quality Evaluation of Andrographis paniculata Capsules Based on Rapid and Accurate LC-ESI-MS/MS Assay of Three Diterpenoids.

Author

Fu S1, Du L2, Yuan Y3, He X2,4.

Publish date

2019 Aug 16

PMID

30572573

Abstract

Andrographis Herba (AH), the dry aerial segments of Andrographis paniculata (Burm.f.) Nees, is a common herbal remedy with bitter properties in traditional Chinese medicine (TCM) theory. Although bitterness is one of the features representing Chinese medicine, it has not been implemented as an index to assess the quality and efficacy of TCM because of peoples’ subjectivity to taste. In this study, 30 batches of AH with different commercial classifications (leaves, stems, or mixtures of both) were collected. Bitterness of AH was quantified by electronic tongue technology. Meanwhile, chemical compositions were characterized through establishing high-performance liquid chromatography fingerprints. The result indicated that the radar curves of the bitterness from different AH commercial classifications displayed different taste fingerprint information. Based on six taste factors, a Principal Component Analysis (PCA) score three-dimensional (3D) plot exhibited a clear grouping trend (R²X, 0.912; Q², 0.763) among the three different commercial classifications. Six compounds (Peaks 2, 3, 4, 6, 7, 8) with positive correlation to bitterness were discovered by a Spearman correlation analysis. Peaks 2, 6, 7, 8 were identified as andrographolide, neoandrographolide, 14-deoxyandrographolide, and dehydroandrographolide, respectively. The electronic tongue can be used to distinguish AH samples with different commercial classifications and for quality evaluation

KEYWORDS

Andrographis Herba; Principal Component Analysis; Spearman correlation analysis; bitter substances; chromatographic fingerprints; electronic tongue

Title

Determination of Bitterness of Andrographis Herba Based on Electronic Tongue Technology and Discovery of the Key Compounds of Bitter Substances.

Author

Zhang X1,2, Wu H3, Yu X4, Luo H5, Lu Y6,7, Yang H8, Li X9, Li Z10, Tang L11, Wang Z12.

Publish date

2018 Dec 19

PMID

30234309

Abstract

ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery

Title

Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis.

Author

Li Y1,2,3, Lin HX1, Wang J1, Yang J1, Lai CJ1, Wang X3,4, Ma BW3,4, Tang JF1, Li Y1,2, Li XL3,4, Guo J1, Gao W3,4,5, Huang LQ1,2.

Publish date

2018 Oct 5


Description :

Neoandrographolide is a diterpenoid from the Andrographis paniculata (Acanthaceae).